Mono-azo acid wool dyestuff



Patented Mar. 14, 1939 UNITED STATES v g 2,150,787 PATENT OFFICE2,150,787 r r MoNo-Azo Acm woor. DYESTUFF No Drawing. Application July2, 1937, Serial No. 151,662. In Germany July 29, 1936 4 Claims.

Our present invention relates to acid wool dyestufis, more particularlyto those of the general formula:

R 5 t on NH-acyl wherein R stands for a member selected from the groupconsisting of aliphatic radiclesand unsub- 15 stituted members of thebenzene series, R1 stands for a member selected from the groupconsisting of aliphatic radicles containing at least six carbon atomsand the cyclohexyl radicle, wherein R and R1 together must contain atleast I0 carbon v atoms, one X means hydrogen and the other a sulfonicacid group, which dyestuffs dye the animal fibers reddish shades of agood fastness. They are particularly valuable by the fact that theytinge in the dyeing process of mixed tissues of wool and cotton thelatter to a very littledegree. The new dyestuffs are obtained bycombining diam-derivatives of aminocompounds of the general formula:

wherein R and Bi have the aforesaid significm tions withacyl-deriv'atives of 1- amino-8-hy droxynaphthalen'e-36- and 4.6disulfonic'acids.

40 The above aminesmay be prepared by starting Example'l 24.7 parts of3-amiri'ohexahydrodiphenyl-4- isobutylether are dissolved in about300p'ar'ts of hot water and 24 parts of concentrated-hydrochloric acid(d=1.19) and the diazotisation is carried out by means of thecorresponding quantity of sodium nitrate at 5 to C. The formedcliagosolution-v is combined at about 10 C. so with an aqueoussolutiomof'53 parts-of 1-(2'5'- dim e t h yl -4 -ch1orobenzenesulfo)-amino- 8 napthol-3.6-disulfonic acid and 34 parts of sodium carbonate;The isolated and dried dyestufi of the formula:

' HaC CH:

CHI

HO NHSO O] SOaH v Example 2 28.1 parts of3-aminohexahydrodiphenyl-lbenzylethe'r are diazotized. The diazosolutionthus obtained is added to a solution of 49 parts of 1-(2-chlorophenoxyacetyl) amino 8 -naphthol-4.6-disulphonic acid. Whenthe'combination has been finished the formed dyestuff of the formula:

no Ne -00035019 H O a S Ha Ha- HQ H,

naphthol-Bfi-disulfonic acid dyestuffs areobamino-8-naphthol-3.6-disulfonic a c i d. Th e tained which dye woolvery bright and fast bluish formed dyestuif of the formula: red shades.

Example 3 M The diazocompound of 24.7 parts of3-aminohexahydro-diphenyli-n-butylether is combined in the presence ofsodium carbonate with 49 parts of 1-(2'-chlorophenoxyacetyl) -amino- 8 rnaphthol-3.6-disulfonic acid. The isolated dyestufi of the formula:

' Cl 0.. NHOQ (311: H035 503E OH:

I H-CH; OH: (I) a. H, l I 0H NH--O0OH:O E

CH: 011; 01 is when dry a red water soluble powder and dyes wool bluishred shades of a good fastness. Hols s0=H Example 6 H The diazocompoundof 26.3 parts of 3-aminoisooktylphenyl-4-isopropylether is combined inH: H: the presence of lime with 53 parts of1-(25'-dimethyl-4'-chlorobenzenesulfo) amino-8 naph- H2 H2thol-3.6-disulfonic acid. The formed dyestufif of the formula:- H1 H.o/OH:

. OH OH is when dry a red powder soluble in water with 1 a red color. Itdyes wool bright red shades fast 0H NH 5 O1 to filling, perspiration andlight. 0

When using as coupling component acetylor benzoyl-1.8-aminonaphthol-3.6-or -4.6-disulfon- Ho S SOH ic acid dyestuffs are obtained exhibitingpure shades and a good fastness.

Example 4 CH1 The diazocompound of 26.7 parts of 3-amino- HaoqfaoHhexahydrodiphenyl-4-phenylether is combined is when dry a red powder,soluble in water with a red color and dyes wool bright and fast bluishred shades.

Similar valuable products are obtained when starting from3-amino-isooktylphenyl-ethylor buthylether.

in the presence of sodium carbonate with 49 parts of 1- 2chlorophenoxyacetyl) -amino-8-naphthol-4.6 disulfonic acid. The formeddyestufl of the formula:

Example 7 The diazocompound of 31.1 parts of3-aminoisookty1phenyl-4-benzy1ether is combined in the presence ofsodium carbonate with 47 parts of 1- (2'-methylphenoxyacetyl)amino-8-naphthol- 3.6-disulfonic acid. The formed dyestufi of the N=N C1formula: H038 OaH Ha Ha H: H: H e r on NHOOUH:O3 Ha v =N o 8 is when drya red water soluble powder and dyes no s 80,11 wool bright red shadesfast to fillin Derspiration and light. HIO 'COHI Example 5 Thediazocompound of 28.3 parts of 3-amino- H'OC OH'isohexylphenyl-4-benzylether is combined at about 5 to 1O C. inthepresence of sodium caris when dry a red water soluble powder and dyesbonate with 40 parts of 1- (2'.5-dichlorobenzoyl) I wool bright and fastred shades.

We claim: 1. Acid wool dyestuffs of the general formula:

R I O HO: X

H: Ha

Ha H2 which dyestufi is when dry a dark red powder soluble in water witha red coloration and dyes wool bright bluish red shades of a goodfastness to filling, perspiration and light.

3. An acid wool dyestuff of the formula:

G1 I H: O OH NH-OO =N CI HaC-(FH which dyestufl is when dry a red watersoluble powder and dyes wool bluish red shades of a good fastness.

4. An acid wool dyestuff of the formula:

which dye stuff is when dry a red powder, soluble in water with a redcolor and dyes wool bright and. fast bluish red shades.

CARL TI-IEO SCHULTIS. ERNST KORTEN.

